A Diradical Approach towards BODIPY-Based Dyes with Intense Near-Infrared Absorption around λ=1100 nm

Yong Ni; Sangsu Lee; Minjung Son; Naoki Aratani; Masatoshi Ishida; Animesh Samanta; Hiroko Yamada; Young-Tae Chang; Hiroyuki Furuta; Dongho Kim; Jishan Wu

doi:10.1002/anie.201511151

A Diradical Approach towards BODIPY-Based Dyes with Intense Near-Infrared Absorption around λ=1100 nm

Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2815-9. doi: 10.1002/anie.201511151. Epub 2016 Jan 25.

Authors

Yong Ni^{1

2}, Sangsu Lee³, Minjung Son³, Naoki Aratani⁴, Masatoshi Ishida⁵, Animesh Samanta², Hiroko Yamada⁴, Young-Tae Chang², Hiroyuki Furuta⁵, Dongho Kim³, Jishan Wu^{6

7}

Affiliations

¹ Department of Chemistry, National University of Singapore, 117543, Singapore, Singapore.
² Laboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium, 138667, Singapore, Singapore.
³ Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 120-749, Korea.
⁴ Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
⁵ Education Center for Global Leaders in Molecular Systems for Devices, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.
⁶ Department of Chemistry, National University of Singapore, 117543, Singapore, Singapore. chmwuj@nus.edu.sg.
⁷ Institute of Materials Research and Engineering, A*STAR, 2 Fusionopolis Way, Innovis, #08-03, 117602, Singapore, Singapore. chmwuj@nus.edu.sg.

PMID: 26804451
DOI: 10.1002/anie.201511151

Abstract

A diradical approach to obtain stable organic dyes with intense absorption around λ=1100 nm is reported. The para- and meta-quinodimethane-bridged BODIPY dimers BD-1 and BD-2 were synthesized and were found to have a small amount of diradical character. These molecules exhibited very intense absorption at λ=1088 nm (ɛ=6.65×10(5) M(-1) cm(-1) ) and 1136 nm (ɛ=6.44×10(5) M(-1) cm(-1) ), respectively, together with large two-photon-absorption cross-sections. Structural isomerization induced little variation in their diradical character but distinctive differences in their physical properties. Moreover, the compounds showed a selective fluorescence turn-on response in the presence of the hydroxyl radical but not with other reactive oxygen species.

Keywords: BODIPY; dyes/pigments; fluorescence; radicals; reactive oxygen species.

Publication types

Research Support, Non-U.S. Gov't